Toward the Total Synthesis of Divergolides C and D

Anastasia Hager; Christian A. Kuttruff; Dominik Hager; Daniel W. Terwilliger; Dirk Trauner

doi:10.1055/s-0033-1338974

Synlett, Table of Contents

Synlett 2013; 24(15): 1915-1920
DOI: 10.1055/s-0033-1338974

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Toward the Total Synthesis of Divergolides C and D

Authors

Anastasia Hager

Fakultät für Chemie und Pharmazie, Ludwig-Maximilians-Universität München, and Munich Center for Integrated Protein Science, Butenandtstrasse 5-13, 81377 München, Germany Email: dirk.trauner@lmu.de
Christian A. Kuttruff

Fakultät für Chemie und Pharmazie, Ludwig-Maximilians-Universität München, and Munich Center for Integrated Protein Science, Butenandtstrasse 5-13, 81377 München, Germany Email: dirk.trauner@lmu.de
Dominik Hager

Fakultät für Chemie und Pharmazie, Ludwig-Maximilians-Universität München, and Munich Center for Integrated Protein Science, Butenandtstrasse 5-13, 81377 München, Germany Email: dirk.trauner@lmu.de
Daniel W. Terwilliger

Fakultät für Chemie und Pharmazie, Ludwig-Maximilians-Universität München, and Munich Center for Integrated Protein Science, Butenandtstrasse 5-13, 81377 München, Germany Email: dirk.trauner@lmu.de
Dirk Trauner*

Fakultät für Chemie und Pharmazie, Ludwig-Maximilians-Universität München, and Munich Center for Integrated Protein Science, Butenandtstrasse 5-13, 81377 München, Germany Email: dirk.trauner@lmu.de

Abstract

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Abstract

The divergolides are a family of structurally unprecedented ansa macrocycles. We describe a synthetic strategy toward divergolides C and D that hinges on the biomimetic diversification of a common intermediate. An advanced precursor that incorporates all the carbon atoms of divergolide C and D is presented, and atropisomerism in a sterically crowded acyl naphthalene is studied.

Key words

natural products - ansamycins - macrolides - divergent synthesis - atropisomerism

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References

References

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Supplementary Material

Supporting Information (PDF)